27. Leadership: Pain Point - Regret
15 Nov 2025 · 12 min
Kenny Chapman’s podcast episode (Leadership in a Nutshell, ep. 27) contrasts two types of pain—the pain of discipline and the pain of regret—arguing that regret’s burden is far heavier. Using mentor quotes (Jim Rohn, Les Brown) and personal anecdotes, Chapman links regret to procrastination and perfectionism, shows how delayed actions (e.g., postponing difficult conversations or personnel decisions) create long-term regret, and urges listeners to choose the short-term pain of discipline over the lasting weight of regret. The episode closes with reflective questions and a call to act now and share the episode.
Chapters
Foreign. Hey, my friend Kenny Chapman here, your host of Leadership in a Nutshell, where we're cracking the code of the driven mind. I'm super excited about today's episode. We are doing the second part of Pain Points, and today we're talking about the pain point of regret, episode 27. Let's rock and roll. So I want to remind you, last week we talked about the pain of discipline. This week we're going to dive into the pain of regret. There's two types of pain. We all try to avoid pain. We have different things that we do psychologically, subconsciously, and consciously when it comes to dealing with pain. Today we're gonna dive into this. But I wanna remind you of the quote that I opened with last week, Jim Rohn, the amazing, phenomenal Jim Rohn said, there are two types of pain you will go through in life. The pain of discipline and the pain of regret. Discipline weighs ounces, while regret weighs tons. Regret weighs tons, ladies and gentlemen. And that's where I want you to really think about today. I want. I want you to think about a time in your own life when you've had an emotional trigger, emotional reference point to experiencing regret. A time in your life when you looked back and said, man, if only. I wish I wouldn't have done that. I wish I. I would. You know, this is a great topic for me because I've conditioned myself, I conditioned my own transformational vocabulary, the conversations that Kenny's subconscious has with his conscious mind, that has with Kenny Chapman as a being where I don't believe in regret, I don't believe in failure. But when I look at the world and I hear how people talk and sound and say different things, sometimes we. We experience different things, right? And in different ways. And we have this emotional. So I think about one of my. One of my phenomenal mentors, very wealthy man, as far as the. The world would say. I will say rich. As. As far as the world would say multi millionaire. Anyway, and so you. You've met people like this where he'll say, now in his 70s, he'll say, you know, I. I just wish that I would have gone to college. And that's fascinating to me. When you're a multimillionaire, you own a ton of real estate, you live the life that you. Freedom of schedule, that you allow yourself to have notice. I say that you allow yourself to have. Many of us have the opportunity to create our own schedules, to have a different relationship with the time and effort economy, but we show up differently in the way that we should show up rather than the way that we want to show up or desire to show up. Right? And so what's fascinating to me is when I ask this man and I say, you know, why. Why do you wish that you would have gone to college? And he said, well, you know, I just think about what I've accomplished in life and what if I would have had a degree? What if I would have learned more? And. And that's sad, in my opinion. That's really. That's one of those tragedies where Les Brown taught me that, you know, the biggest. The biggest challenge in life is the. The pain of people going to the grave with their goals and their dreams and the. And the relationships that they could have had and the businesses that they could have been involved in and the leadership skills and influence that they could have shown up with and for in the world. And so I want you to just think about this, because for me, that's a great mirror, because there's. I don't have a college education. I went to a semester of college, but I definitely don't practice my education of college on a daily basis. I might reference, like, yeah, I went to, if any, if college taught me anything, I wasn't as good of a baseball player as I thought I was. How about that? And I didn't like. Check this out. I didn't like speech and debate. One of my most difficult classes in college, that short stint I had was speech and debate. And now look, I get paid thousands and thousands of dollars to be a keynote speaker and change and influence and impact lives, have my own podcast, all these different incredible things, right? So I want you to think about regret because it's very powerful. As long as this gentleman holds in his heart, in his mind and his body and his spirit, that he wishes that he would have gone and done that, then he's robbing himself from the gratitude and ultimately the fulfillment that he deserves in his life at this moment in time today. Now, as we think about regret, where does it show up? Like we talked about last week, we do more to avoid pain than we do to gain pleasure. So it's a fascinating thing when we look at this pain thing. Oh, I want to avoid it. I want to avoid it. And yet sometimes it's a necessary component of the school of success. Sometimes it's absolutely 100% necessary for us to experience some what the world would call pain in order to get what results that we want and ultimately live the life that we truly desire and deserve. I love when John Maxwell Once said, most people want to avoid pain, and discipline is usually painful. Remember last week we talked about discipline being one of the types of pain. Think about that. Today we're diving into regret. But I want to remind you that you're gonna have pain. So let's choose discipline, and let's avoid this regret part that we have. And so when we think about, well, sometimes, you know, it's. It's painful. Kenny, guess what? It's not as painful to do what you want to do the way that you want to, to learn the things that you need to learn to, quote, fail in the world. And I say quote, because there is no such thing. But when you roll out a new program at your company, when you're a new leader and you hold a meeting and you don't have people's attention, you roll out a pay plan that doesn't work. You have a marketing campaign that falls on its face, you roll out a new sales process, and it doesn't get the results you want. That's painful, right? Or is it? Guess what? It's not near as painful as continuing to do what you always have done. Getting results you've always gotten, but actually worse results than you can get. So the reality is the pain of staying the same is ultimate. And I believe that's the ultimate regret. When we stay where we are now, I want to. I want you to think about your own regret for a moment. And one of the biggest causes of regret is this thing that we call procrastination. I work with my one on one clients around procrastination and perfection all the time. Perfection's the number one productivity killer in the world, and it creates a ton of regret in the world. Why? Because I won't do something. I won't take that next step. I won't roll the dice. I won't get in the game until everything is lined up and everything is perfect. That leads to procrastination. Procrastination leads to no action. No action leads to regret. You see how we're. How we're taking this walk? You see how this is working here, my friends? That's ultimately what it's all about. So let me ask you this. I know you don't want to be a procrastinator. You wouldn't be on the line. You wouldn't be sharing this time and energy and space with us in the leadership, in a nutshell community if you were all about just hanging out and waiting for the world to show up and serve it to you on a silver platter. I know you don't want to be a procrastinator, so ask yourself, what have I been putting off lately? What are some things that I need to do? What is that difficult conversation I need to have with a team member or a loved one or even my spouse? What's something that you keep on moving? You've got your to do list, and there's a task on it that you've been moving forward and moving to the next day and moving, you know, what life are you continuing to lead? Because you haven't said yes to your greatest self. You haven't taken that step and gone, man, I'm not going to regret not stepping into my greatness. These seem to be little things, but they kind of compile and compile, and ultimately we get that feeling inside, which is actually a feeling of regret, that discomfort, that ultimate pain, right? And ultimately, what you always see and you hear, and I study greatness, I study human performance. And I love interviewing people that are in their 70s and their 80s, and when they reflect on their lives and they talk about the things that they wish they would have done differently, it's never action, my friends. It's always that they wish they would have done more, seen more, loved more, engaged in community more, made more money, sometimes become richer, Right? You go, oh, wait a minute, Kenny, you're going to go, yes, I'm going to go there. Because wealth creates opportunity. That's all it is. This is the road of regret, when you deny yourself of what you truly want. So, you know, let's think about this as we kind of wrap up our time together. I just wanted to hit you quick and direct and focus on regretting your life. And if you have some to this point, that's okay. I'm not saying minimize it. I'm not saying justify it. I'm saying call it what it is. Look it in the face, directly decide today, directly commit today, that you're not going to continue to allow regret into your life. You've got pain of discipline. You've got pain of regret. It's a decision, my friends, and it's a decision that must be made moment by moment. It's got to be made daily, every day. You've got to make a decision. Am I going to deal with discipline or am I going to deal with regret? The difficult path is always something that's worth us taking on and following. Right. Ultimately, you know, my mentor, Les Brown, used to talk about, you know, live life the hard way and life will become easy. Live life the easy way. And life will become hard. Now, when I first heard that, I'm like, well, les, I want to live my life with ease, joy and glory. I don't want to choose pain. I don't want to choose hardship. I don't want to live hard today. And you go, wait a minute. What's the context of this, Kenny? So I want to leave you with that today. I want you to just really think about what is something that I've been putting off. Those questions I asked you before, what am I putting off? What are the book that I wanted to read or listen to? What's the strategy that I want to implement? What's the conversation I need to have? Here's the reality. When I ask leaders, when they, oh, man, I made a difficult decision. I finally let so and so go. Fill in the blank. You've got your so and so right now as we're talking today, I finally let so and so go. I finally promoted other so and so. Whatever it is, I'll ask this question. How long have you known? Well, what do you mean? How long have you known that you needed to let so and so go? Oh, man. And they kind of think and they respond and they look. And you can see their physiology. If it's. If it's in a video call or if you were in person and they're like, yeah, I've probably known for 18 months. I've probably known a year. I've probably known five years, whatever that is. Don't put yourself in the place of regret, my friend. Stop putting off until tomorrow what you can do today. The reality is, are you going to have pain in your life? Sure you are. The last two weeks, we've talked about two types of pain, discipline or regret. Which one do you want to choose? I certainly hope you will not choose regret. That's the reality. You get a choice. I'm sure by now you've subscribed. If you're one of our newer listeners, make sure that you subscribe. If you and do this one thing today, send this episode to somebody you know. You do not want people going to their grave with regret. Share this episode with a loved one. And until we talk, my friends, make it a better than fantastic day. This is episode 27, Leadership in a Nutshell. I'm Kenny Chapman, your host. Have a great one, everybody.